phosphoric acid 1-cyano-2,2-dimethylpropyl ester diethyl ester | 70525-84-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: phosphoric acid 1-cyano-2,2-dimethylpropyl ester diethyl ester
• 英文别名: 2-(Diethylphosphonooxy)-3,3-dimethylbutanenitrile；1-Cyan-2,2-dimethylpropyldiethylphosphat；1-Cyano-2,2-dimethylpropyl diethyl phosphate；(1-cyano-2,2-dimethylpropyl) diethyl phosphate
• CAS: 70525-84-7
• 化学式: C₁₀H₂₀NO₄P
• 分子量: 249.247
• InChiKey: ANLQUQNWWKYTED-UHFFFAOYSA-N

物化性质

• 沸点：
  101-102 °C(Press: 0.2 Torr)
• 密度：
  1.5025 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  膦酸,(2,2-二甲基-1-羰基丙基)-,二乙基酯 、 氰化钾 在 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.08h， 以79%的产率得到phosphoric acid 1-cyano-2,2-dimethylpropyl ester diethyl ester
  参考文献：
  名称：

  Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state

  摘要：

  Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate-phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents furnished cyanohydrin O-phosphates in good yields. For the high yield formation of cyanohydrin O-phosphates from arylphosphonates THF should be used and from alkylphosphonates DME was used. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.036

文献信息

• Cyano-Phosphorylation of Aldehydes Catalyzed by a Nucleophilic N-Heterocyclic Carbene
  作者：Yoshimasa Fukuda、Yuka Maeda、Kazuhiro Kondo、Toyohiko Aoyama

  DOI：10.1248/cpb.54.397

  日期：——

  The first method for cyano-phosphorylation of aldehydes with diethyl cyanophosphonate in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and KOt-Bu, as a nucleophilic catalyst, is described.

  首次介绍了在由 1,3-双(2,4,6-三甲基苯基)氯化咪唑和 KOt-Bu 制备的 N-杂环碳烯作为亲核催化剂存在下，氰基膦酸二乙酯对醛进行氰基磷化的方法。
• Pudovik,A.N. et al., Journal of general chemistry of the USSR, 1979, vol. 49, p. 225 - 231
  作者：Pudovik,A.N. et al.

  DOI：——

  日期：——
• A convenient and improved preparation of Cyano phosphates
  作者：Irene Micó、Carmen Nájera

  DOI：10.1016/s0040-4020(01)85749-5

  日期：1993.1

  Cyano phosphates derived from aldehydes or ketones are prepared in good yields using lithium cyanide in DMF and diethyl chlorophosphate as phosphorylating agent.
• PUDOVIK A. N.; POMAHOB G. V.; NAZMUTDINOV R. YA., ZH. OBSHCH. XIMII, 1979, 49, HO 2, 257-264
  作者：PUDOVIK A. N.、 POMAHOB G. V.、 NAZMUTDINOV R. YA.

  DOI：——

  日期：——
• Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state
  作者：Ayhan S. Demir、Ömer Reis、Ilker Esiringü、Barbaros Reis、Sehriban Baris

  DOI：10.1016/j.tet.2006.10.036

  日期：2007.1

  Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate-phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents furnished cyanohydrin O-phosphates in good yields. For the high yield formation of cyanohydrin O-phosphates from arylphosphonates THF should be used and from alkylphosphonates DME was used. (c) 2006 Elsevier Ltd. All rights reserved.